I recently installed potato on a spare box and upgraded it to woody just to see how it went. Mostly painless, but not totally.
I made a point to install debconf and apt-utils before doing the regular dist-upgrade. The woody packages complained about several scripts which were part of potato installs which I did not change. These were /etc/pam.d/login /etc/manpath.config /etc/lynx.cfg among others. It asked me if I wanted to diff, keep original, install new, etc. I chose to install the new one. The default is to keep the original, which seems to me to be wrong. Why would I want a new package with an old config file? dist-upgrade did not upgrade my kernel, it left me at 2.2. I had to pick and choose a 2.4 kernel separately. I found the instructions about the initrd line to be very strange, why doesn't it just modify lilo.conf for me? ~mark